This chapter is from the book

Challenging Questions

To understand how to handle tough questions, let’s begin with the reason people ask such questions. Journalists such as Katie Couric and Chris Wallace (the son of the legendary provocative interrogator Mike Wallace) ask tough questions because, being familiar with the classical art of drama, they know that conflict creates drama. Aristotle 101.

One of the most regularly occurring examples of journalistic baiting is in presidential press conferences. Every U.S. president, regardless of party affiliation, periodically faces the slings and arrows of tough questions from the White House press corps. One such exchange took place on June 23, 2009. In a press briefing following violent demonstrations in Teheran, Iran, President Barack Obama said

The United States and the international community have been appalled and outraged by the threats, the beatings, and imprisonments of the last few days. I strongly condemn these unjust actions, and I join with the American people in mourning each and every innocent life that is lost.

He then opened the floor to NBC’s Chuck Todd, who asked

TODD: Mr. President, I want to follow up on Iran. You have avoided twice spelling out consequences. You’ve hinted that there would be, from the international community, if they continue to violate—you said violate these norms. You seem to hint that there are human rights violations taking place.

THE PRESIDENT: I’m not hinting. I think that when a young woman gets shot on the street when she gets out of her car, that’s a problem.

TODD: Then why won’t you spell out the consequences that the Iranian—

THE PRESIDENT: Because I think, Chuck, that we don’t know yet how this thing is going to play out. I know everybody here is on a 24-hour news cycle. I’m not.

TODD: But shouldn’t—I mean, shouldn’t the world and Iran—

THE PRESIDENT: Chuck, I answered—

TODD: —but shouldn’t the Iranian regime know that there are consequences?

THE PRESIDENT: I answered the question, Chuck, which is that we don’t yet know how this is going to play out. 1.1

Another tense exchange occurred on March 1, 2013. In a press briefing following severe cuts made in the federal budget, President Obama said

None of this is necessary. It’s happening because of a choice that Republicans in Congress have made. They’ve allowed these cuts to happen because they refuse to budge on closing a single wasteful loophole to help reduce the deficit.

He then opened the floor to the Associated Press’s Julie Pace who asked

Thank you, Mr. President. How much responsibility do you feel like you bear for these cuts taking effect? And is the only way to offset them at this point for Republicans to bend on revenue, or do you see any alternatives?

In his response, Obama said

But what is true right now is that the Republicans have made a choice that maintaining an ironclad rule that we will not accept an extra dime’s worth of revenue makes it very difficult for us to get any larger comprehensive deal. And that’s a choice they’re making. They’re saying that it’s more important to preserve these tax loopholes than it is to prevent these arbitrary cuts.

which prompted the reporter to repeat her question:

PACE: It sounds like you’re saying that this is a Republican problem and not one that you bear any responsibility for.

The President of the United States can dismiss Chuck Todd with, “I answered the question, Chuck!” or Julie Pace by turning her question back to her for an answer, but you do not have that luxury. In business, you must respond fully to your audience whether that person is a customer, an investor, or a manager.

To do that, you have to understand the reason business people ask challenging questions. Is it because they are mean-spirited? Perhaps. Is it because they want to test your mettle? Perhaps. More likely it is because when you are presenting your position, you are asking your opposite party or parties, your target audience, to change, which is just the case in almost every decisive communication in business—as well as in those other walks of life. Most human beings are resistant to change, and so they kick the tires.

You are the tires.

The most mission-critical of all business presentations is the initial public offering (IPO) road show, a form of communication I have had the privilege and opportunity to coach for nearly 600 companies, among them Cisco Systems, Intuit, Yahoo!, Dolby Laboratories, eBay, and most recently, Trulia, the successful real estate search engine company. In those road show pitches, presenters ask their investor audiences to change: to buy a stock that never existed. In fact, when a company offers shares to the public for the first time, the U.S. Securities and Exchange Commission mandates that they specifically state the risk in print. The offering company must make available a prospectus containing a boilerplate sentence that reads, “There has been no prior public market for the company’s common stock.” In other words, caveat emptor—or, “Invest at your own risk.” As a result, when a company’s executive teams take their presentations on the road, they are inevitably assaulted with challenging questions from their potential investors.

Although the stakes in an IPO road show are exceedingly high—in the tens or hundreds of millions of dollars—the character of the challenge is no different from that of potential customers considering a new product, potential partners considering a strategic relationship, pressured managers considering a request for additional expenditures, concerned citizens considering a dark horse candidate, a human resources manager considering a new employee, or even affluent contributors considering a donation to a nascent, not-for-profit cause.

The inherent challenge in these circumstances is compounded in presentation settings where the intensity level is raised by several additional factors:

Public exposure. The risk of a mistake is magnified in large groups.

Group dynamics. The more people in the audience, the more difficult it is to maintain control.

One against many. Audiences have an affinity bond among themselves and apart from the presenter or speaker.

The result is open season on the lone figure spotlighted at the front of the room, who then becomes fair game for a volley of even more challenging questions.

How then, to level the playing field? How then, to give the presenter the weapons to withstand the attack?

The answer lies in the David versus Goliath match, in which a mere youth was able to defeat a mighty giant using only a stone from a slingshot. This biblical parable has numerous equivalents in military warfare. History abounds with examples in which small, outnumbered, under-equipped units were able to combat vastly superior forces by using adroit maneuvers and clever defenses. Remember the Alamo, but also remember Thermopylae, Masada, Agincourt, the Bastille, Stalingrad, the Battle of the Bulge, Iwo Jima, and the Six-Day War. All these legendary battles share one common denominator: leverage, or the use of agility to counter force.